1. Field of the Invention
This invention relates generally to polydioxaborines. More particularly, it relates to polymers that comprise a 1,3,2-dioxaborine group in the side chain and/or the main chain, and to methods of making them using the corresponding monomers. Preferred polymers have semiconducting properties and, more preferably, are compatible with modem processing techniques such as precision injection molding, extrusion, spin coating and casting.
2. Description of the Related Art
Dioxaborines contain a core six-membered heterocyclic ring with the general formula C3O2B. Various dioxaborine-containing compounds have been reported, see, e.g., Reynolds et al., “The Reactions of 2,2-Difluoro-4-methylnaptho[1,2-e]-1,3,2-dioxaborin and Its [2,1-e] Isomer with N,N-Dimethylformamide,” J. Heterocyclic Chem., vol. 6, pp. 375-377, (1969); Narula, et al., “Preparation and Characterization of Salts Containing Cations of Tricoordinate Boron,” Inorg. Chem., vol. 23, pp. 4147-4152 (1984); Hartmann, “Ein Einfacher Weg zu Neuartigen Borhaltigen Spiroverbindungen,” J. Prakt. Chemie, vol. 328, no. 5, pp 755-762 (1986); Görlitz, et al., “On the Formation and Solvolysis of 4-Aryl-2,2-difluoro-6-methyl-1,3,2-(2H)-dioxaborines,” Heteroatom Chemistry, vol. 8, no. 2, pp. 147-155 (1997); Reynolds, et al., “Styryl Dyes Derived from Bis Boron Diketonates,” J. Heterocyclic Chem., vol. 622 pp. 657-659, (1985); Reynolds, et al., “Synthesis of Chromones,” J. Heterocyclic Chem., vol. 16, pp 369-370 (1979); VanAllan, et al., “The Reactions of 2,2-Difluoro-4-methylnaptho[1,2-e]-1,3,2-dioxabroin and Its [2,1-e] Isomer with Carbonyl Compounds and with Aniline,” J. Heterocyclic Chem., vol. 6, pp. 29-35, (1969); and Bally, et al., “Reaction of Beta-Ketoenols with Diphenylborinic Esters,” Tet. Lett., no. 44, pp. 3929-3931, (1965).
Mixtures of 1,3,2(2H)-dioxaborine dyes and poly(methyl)methacrylate have been reported, see Kammler, et al., “Second-order Optical Non-linearity of New 1,3,2-(2H)-Dioxaborine Dyes,” J. Chem. Soc., Faraday Trans., vol. 92, no. 6, pp. 945-947 (1996). However, the dioxaborine group was not attached to the polymer.